Synthesis, Characterization, and Reaction Chemistry of tert-Butyl Hypofluorite

Evan H. Appelman, David French, Eyal Mishani, Shlomo Rozen

Research output: Contribution to journalArticlepeer-review

Abstract

tert-Butyl hypofluorite ((CH3)3COF) can be synthesized by the low-temperature reaction of elemental fluorine with tert-butyl alcohol dissolved in propionitrile or acetonitrile. The isolated compound, which melts around –94 °C and has an extrapolated boiling point of about +40 °C, has been characterized by mass, NMR, and IR spectrometry. The 19F NMR shift of +67 ppm lies between the corresponding shifts of HOF and CH3OF and implies a rather high O-F bond energy. Although sterically crowded, tert-butyl hypofluorite adds to olefins to form β-fluoro-tert-butoxy compounds. Addition is mainly in an anti mode, and the regioselectivity corresponds to the action of a hitherto unknown tert-butoxylium electrophile. Also formed are adducts containing F and CH2CN, the latter deriving from the acetonitrile solvent.

Original languageEnglish
Pages (from-to)1379-1382
Number of pages4
JournalJournal of the American Chemical Society
Volume115
Issue number4
DOIs
StatePublished - 1 Feb 1993

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